Fucosterol (BioDeep_00000279493)

Secondary id: BioDeep_00000000530, BioDeep_00000006996

PANOMIX_OTCML-2023

代谢物信息卡片

(24E)-24-n-propylidenecholesterol;(3beta,24E)-stigmasta-5,24(28)-dien-3-ol;(E)-stigmasta-5,24(28)-dien-3beta-ol;24E-ethylidene-cholest-5-en-3beta-ol;fucosterin;trans-24-ethylidenecholesterol

化学式: C29H48O (412.37049579999996)
中文名称: 岩皂甾醇, 岩皂甾醇
谱图信息: 最多检出来源 Homo sapiens(blood) 0.17%

分子结构信息

SMILES: C/C=C(C(C)C)/CC[C@@H](C)[C@H]1CC[C@@]2([H])[C@]3([H])CC=C4CC(O)CC[C@]4(C)[C@@]3([H])CC[C@]12C
InChI: InChI=1S/C29H48O/c1-7-21(19(2)3)9-8-20(4)25-12-13-26-24-11-10-22-18-23(30)14-16-28(22,5)27(24)15-17-29(25,26)6/h7,11,19-20,22-23,25-27,30H,8-10,12-18H2,1-6H3/b21-7-

描述信息

A 3beta-sterol consisting of stigmastan-3beta-ol with double bonds at positions 5 and 24(28).
(3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol belongs to stigmastanes and derivatives class of compounds. Those are sterol lipids with a structure based on the stigmastane skeleton, which consists of a cholestane moiety bearing an ethyl group at the carbon atom C24 (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol can be found in horseradish tree and sunflower, which makes (3b,5a,24(28)e)-stigmasta-7,24(28)-dien-3-ol a potential biomarker for the consumption of these food products.
Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1].
Fucosterol is a sterol isolated from algae, seaweed or diatoms.?Fucosterol exhibits various biological activities, including antioxidant, anti-adipogenic, blood cholesterol reducing, anti-diabetic and anti-cancer activities[1][2]. Fucosterol regulates adipogenesis via inhibition of?PPARα?and?C/EBPα?expression and can be used for anti-obesity agents development research[1].

同义名列表

16 个代谢物同义名

Fucosterol; 24Z-ethylidene-cholest-5-en-3-ol; (24E)-24-N-propylidenecholesterol; Stigmasta-7,24(28)-dien-3-ol; (3S,8S,9S,10R,13R,14S,17R)-17-[(E,1R)-4-isopropyl-1-methyl-hex-4-enyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3S,8S,9S,10R,13R,14S,17R)-17-[(E,1R)-4-isopropyl-1-methylhex-4-enyl]-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; (3S,8S,9S,10R,13R,14S,17R)-10,13-dimethyl-17-[(E,2R)-5-propan-2-ylhept-5-en-2-yl]-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-ol; 24-Isoethylidenecholest-5-en-3beta-ol, delta(5)-avenasterol; Stigmasta-5,24(28)-dien-3-ol, (3beta,24E)-; Stigmasta-5,24-dien-3beta-ol; Fucosterin; 17605-67-3; C08817; (24E)-24-n-propylidenecholesterol;(3beta,24E)-stigmasta-5,24(28)-dien-3-ol;(E)-stigmasta-5,24(28)-dien-3beta-ol;24E-ethylidene-cholest-5-en-3beta-ol;fucosterin;trans-24-ethylidenecholesterol; (24E)-stigmasta-5,24(28)-dien-3beta-ol; ST 29:2;O

数据库引用编号

19 个数据库交叉引用编号

ChEBI: CHEBI:27865
ChEBI: CHEBI:173015
KEGG: C08817
PubChem: 5283635
PubChem: 5281328
PubChem: 86747
ChEMBL: CHEMBL519971
LipidMAPS: LMST01040255
LipidMAPS: LMST01040121
MetaCyc: CPD-4127
foodb: FDB021844
CAS: 17605-67-3
PMhub: MS000020218
MetaboLights: MTBLC27865
PubChem: 11010
KNApSAcK: C00003653
3DMET: B02435
NIKKAJI: J9.102B
medchemexpress: HY-N4103

分类词条

代谢反应

0 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(0)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(0)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

183 个相关的物种来源信息

33090 枸杞子: -
33090 昆布: -
63409 Ulva linza:
63410 Ulva lactuca:
111617 Ulva fasciata: 10.1016/0031-9422(92)80435-H
76317 Caulerpa racemosa: 10.1016/0031-9422(92)80435-H
76313 Caulerpa taxifolia: 10.1016/0031-9422(92)80435-H
2876 Dictyota dichotoma:
499615 Canistrocarpus cervicornis: 10.1016/S0031-9422(00)90430-8
143162 Sargassum filipendula: 10.1016/S0031-9422(00)90430-8
531973 Dictyopteris delicatula: 10.1016/S0031-9422(00)90430-8
381676 Dictyota mertensii: 10.1016/S0031-9422(00)90430-8
2651306 Ellisella paraplexauroides: 10.1016/0305-0491(92)90235-J
238994 Leptogorgia piccola: 10.1016/0305-0491(92)90235-J
239013 Leptogorgia violetta: 10.1016/0305-0491(92)90235-J
1528112 Leptogorgia viminalis: 10.1016/0305-0491(92)90235-J
3107 Hydrodictyon reticulatum: 10.1016/0031-9422(91)80079-G
52969 Ascophyllum nodosum: 10.1016/0031-9422(83)83040-4
49266 Fucus vesiculosus: 10.1016/0031-9422(83)83040-4
981110 Alitta succinea: 10.1016/0039-128X(94)90124-4
35128 Thalassiosira pseudonana:
49261 Thalassiosira eccentrica: 10.1016/0031-9422(88)80200-0
3728 Sinapis alba: 10.1016/S0031-9422(00)84080-7
83371 Detonula confervacea: 10.1016/0031-9422(91)83634-W
29204 Cyclotella cryptica: 10.1016/0031-9422(91)83634-W
1577725 Conticribra weissflogii: 10.1016/0031-9422(91)83634-W
40811 Nitellopsis obtusa: 10.1021/NP50076A041
77624 Lamprothamnium papulosum: 10.1021/NP50076A041
31298 Chara australis: 10.1021/NP50076A041
4054 Panax ginseng: 10.1007/BF02645749
44588 Panax quinquefolius: 10.1007/BF02645749
51239 Vanilla planifolia: 10.1007/S11746-998-0009-8
120407 Dictyuchus monosporus: 10.1016/S0031-9422(00)80786-4
200961 Trigonella balansae: 10.1016/0305-1978(95)00105-0
200965 Trigonella corniculata: 10.1016/0305-1978(95)00105-0
200963 Trigonella caerulea: 10.1016/0305-1978(95)00105-0
200951 Melilotus indicus: 10.1016/0305-1978(95)00105-0
78533 Trigonella cretica: 10.1016/0305-1978(95)00105-0
119381 Trigonella calliceras: 10.1016/0305-1978(95)00105-0
78534 Trigonella foenum-graecum: 10.1016/0305-1978(95)00105-0
439534 Padina gymnospora: 10.1016/S0031-9422(00)80787-6
531984 Padina pavonica: 10.1016/S0031-9422(00)80787-6
29722 Amaranthus tricolor: 10.1006/BIOO.1993.1007
353996 Mansoa alliacea: 10.1006/BIOO.1993.1007
3702 Arabidopsis thaliana: 10.1016/0031-9422(93)85095-9
397682 Diplopterygium glaucum: 10.1248/CPB.41.624
3274 Gleichenia japonica: 10.1248/CPB.41.624
4222 Carthamus tinctorius: 10.1002/PTR.2650080603
68564 Petrosia ficiformis: 10.1016/0039-128X(80)90095-1
942674 Amphilectus fucorum: 10.1016/S0040-4020(01)85914-7
458493 Ectyoplasia ferox: 10.1007/BF02535143
80912 Kalanchoe petitiana: 10.1016/0031-9422(91)83027-I
2171618 Magallana gigas: 10.1016/S0305-0491(97)00269-1
29159 Crassostrea gigas: 10.1016/S0305-0491(97)00269-1
569448 Salpa thompsoni: 10.1248/CPB.34.4562
295239 Dragmacidon lunaecharta: 10.1016/0039-128X(81)90070-2
590725 Cystoseira barbata: 10.1016/S0031-9422(96)00588-2
75689 Ulva rigida: 10.1016/S0031-9422(00)83106-4
590727 Sargassum fusiforme:
4577 Zea mays: 10.1016/0031-9422(84)83081-2
7461 Apis cerana: 10.1371/JOURNAL.PONE.0175573
3116 Ulva intestinalis: 10.1016/S0031-9422(00)82185-8
4146 Olea europaea: 10.1007/BF02541591
105407 Ecklonia cava: 10.1016/J.BMC.2009.01.031
3120 Ulva pertusa: 10.1007/S10600-010-9760-9
111616 Ulva australis: 10.1007/S10600-010-9760-9
177573 Hymeniacidon perlevis: 10.1016/S0040-4020(01)88936-5
6058 Haliclona oculata: 10.1139/V85-398
127999 Tanacetum parthenium:
127557 Turbinaria conoides:
93837 Silvetia siliquosa: 10.1007/BF02975115
358797 Sarcophyton crassocaule: 10.1021/NP990205P
4555 Setaria italica: 10.1271/BBB.63.1800
178554 Xestospongia testudinaria: 10.1021/JA00009A046
6395 Eisenia bicyclis: 10.1016/0031-9422(90)85305-Y
87150 Fucus virsoides: 10.1515/ZNB-1994-0923
86657 Turbinaria ornata: 10.1055/S-2006-957772
381694 Stypopodium flabelliforme: 10.1016/0031-9422(92)83610-B
3885 Phaseolus vulgaris: 10.1016/0031-9422(88)83160-1
91052 Durvillaea potatorum: 10.1016/S0031-9422(00)90336-4
318066 Tridax procumbens: 10.1016/0031-9422(88)83120-0
127572 Sargassum siliquastrum: 10.1016/0031-9422(92)80262-D
3015 Sargassum: 10.4103/0974-8490.85000
499621 Dictyota spiralis: 10.1016/J.TET.2009.10.081
499618 Dictyota fasciola: 10.1016/J.TET.2009.10.081
156996 Dictyopteris divaricata: 10.1021/NP040099D
39984 Bruguiera gymnorhiza: 10.1016/S0031-9422(00)81558-7
1134458 Avicennia officinalis: 10.1016/S0031-9422(00)81558-7
328098 Acanthus ilicifolius: 10.1016/S0031-9422(00)81558-7
189428 Flabellia petiolata: 10.1080/10575630008043770
325645 Tydemania expeditionis: 10.1016/J.FITOTE.2012.04.019
126577 Sargassum carpophyllum: 10.1080/10286020290027362
63409 Ulva linza:
63410 Ulva lactuca:
111617 Ulva fasciata: 10.1016/0031-9422(92)80435-H
76317 Caulerpa racemosa: 10.1016/0031-9422(92)80435-H
76313 Caulerpa taxifolia: 10.1016/0031-9422(92)80435-H
2876 Dictyota dichotoma:
499615 Canistrocarpus cervicornis: 10.1016/S0031-9422(00)90430-8
143162 Sargassum filipendula: 10.1016/S0031-9422(00)90430-8
531973 Dictyopteris delicatula: 10.1016/S0031-9422(00)90430-8
381676 Dictyota mertensii: 10.1016/S0031-9422(00)90430-8
2651306 Ellisella paraplexauroides: 10.1016/0305-0491(92)90235-J
238994 Leptogorgia piccola: 10.1016/0305-0491(92)90235-J
239013 Leptogorgia violetta: 10.1016/0305-0491(92)90235-J
1528112 Leptogorgia viminalis: 10.1016/0305-0491(92)90235-J
3107 Hydrodictyon reticulatum: 10.1016/0031-9422(91)80079-G
52969 Ascophyllum nodosum: 10.1016/0031-9422(83)83040-4
49266 Fucus vesiculosus: 10.1016/0031-9422(83)83040-4
981110 Alitta succinea: 10.1016/0039-128X(94)90124-4
35128 Thalassiosira pseudonana:
49261 Thalassiosira eccentrica: 10.1016/0031-9422(88)80200-0
3728 Sinapis alba: 10.1016/S0031-9422(00)84080-7
83371 Detonula confervacea: 10.1016/0031-9422(91)83634-W
29204 Cyclotella cryptica: 10.1016/0031-9422(91)83634-W
1577725 Conticribra weissflogii: 10.1016/0031-9422(91)83634-W
40811 Nitellopsis obtusa: 10.1021/NP50076A041
77624 Lamprothamnium papulosum: 10.1021/NP50076A041
31298 Chara australis: 10.1021/NP50076A041
4054 Panax ginseng: 10.1007/BF02645749
44588 Panax quinquefolius: 10.1007/BF02645749
51239 Vanilla planifolia: 10.1007/S11746-998-0009-8
120407 Dictyuchus monosporus: 10.1016/S0031-9422(00)80786-4
200961 Trigonella balansae: 10.1016/0305-1978(95)00105-0
200965 Trigonella corniculata: 10.1016/0305-1978(95)00105-0
200963 Trigonella caerulea: 10.1016/0305-1978(95)00105-0
200951 Melilotus indicus: 10.1016/0305-1978(95)00105-0
78533 Trigonella cretica: 10.1016/0305-1978(95)00105-0
119381 Trigonella calliceras: 10.1016/0305-1978(95)00105-0
78534 Trigonella foenum-graecum: 10.1016/0305-1978(95)00105-0
439534 Padina gymnospora: 10.1016/S0031-9422(00)80787-6
531984 Padina pavonica: 10.1016/S0031-9422(00)80787-6
29722 Amaranthus tricolor: 10.1006/BIOO.1993.1007
353996 Mansoa alliacea: 10.1006/BIOO.1993.1007
3702 Arabidopsis thaliana: 10.1016/0031-9422(93)85095-9
397682 Diplopterygium glaucum: 10.1248/CPB.41.624
3274 Gleichenia japonica: 10.1248/CPB.41.624
4222 Carthamus tinctorius: 10.1002/PTR.2650080603
68564 Petrosia ficiformis: 10.1016/0039-128X(80)90095-1
942674 Amphilectus fucorum: 10.1016/S0040-4020(01)85914-7
458493 Ectyoplasia ferox: 10.1007/BF02535143
80912 Kalanchoe petitiana: 10.1016/0031-9422(91)83027-I
2171618 Magallana gigas: 10.1016/S0305-0491(97)00269-1
29159 Crassostrea gigas: 10.1016/S0305-0491(97)00269-1
569448 Salpa thompsoni: 10.1248/CPB.34.4562
295239 Dragmacidon lunaecharta: 10.1016/0039-128X(81)90070-2
590725 Cystoseira barbata: 10.1016/S0031-9422(96)00588-2
75689 Ulva rigida: 10.1016/S0031-9422(00)83106-4
590727 Sargassum fusiforme:
4577 Zea mays: 10.1016/0031-9422(84)83081-2
7461 Apis cerana: 10.1371/JOURNAL.PONE.0175573
3116 Ulva intestinalis: 10.1016/S0031-9422(00)82185-8
4146 Olea europaea: 10.1007/BF02541591
105407 Ecklonia cava: 10.1016/J.BMC.2009.01.031
3120 Ulva pertusa: 10.1007/S10600-010-9760-9
111616 Ulva australis: 10.1007/S10600-010-9760-9
177573 Hymeniacidon perlevis: 10.1016/S0040-4020(01)88936-5
6058 Haliclona oculata: 10.1139/V85-398
127999 Tanacetum parthenium:
127557 Turbinaria conoides:
93837 Silvetia siliquosa: 10.1007/BF02975115
358797 Sarcophyton crassocaule: 10.1021/NP990205P
4555 Setaria italica: 10.1271/BBB.63.1800
178554 Xestospongia testudinaria: 10.1021/JA00009A046
6395 Eisenia bicyclis: 10.1016/0031-9422(90)85305-Y
87150 Fucus virsoides: 10.1515/ZNB-1994-0923
86657 Turbinaria ornata: 10.1055/S-2006-957772
381694 Stypopodium flabelliforme: 10.1016/0031-9422(92)83610-B
3885 Phaseolus vulgaris: 10.1016/0031-9422(88)83160-1
91052 Durvillaea potatorum: 10.1016/S0031-9422(00)90336-4
318066 Tridax procumbens: 10.1016/0031-9422(88)83120-0
127572 Sargassum siliquastrum: 10.1016/0031-9422(92)80262-D
3015 Sargassum: 10.4103/0974-8490.85000
499621 Dictyota spiralis: 10.1016/J.TET.2009.10.081
499618 Dictyota fasciola: 10.1016/J.TET.2009.10.081
156996 Dictyopteris divaricata: 10.1021/NP040099D
39984 Bruguiera gymnorhiza: 10.1016/S0031-9422(00)81558-7
1134458 Avicennia officinalis: 10.1016/S0031-9422(00)81558-7
328098 Acanthus ilicifolius: 10.1016/S0031-9422(00)81558-7
189428 Flabellia petiolata: 10.1080/10575630008043770
325645 Tydemania expeditionis: 10.1016/J.FITOTE.2012.04.019
126577 Sargassum carpophyllum: 10.1080/10286020290027362
33090 Plants: -

在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：

PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。

点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。

文献列表

Pengrui Wang, Junfang Zhang, Na Zhan, Shuang Yang, Mingming Yu, Hongbing Liu. The pharmacokinetic characteristics and excretion studies of fucosterol from Sargasssum fusiforme in rats. Biomedical chromatography : BMC. 2022 Apr; 36(4):e5309. doi: 10.1002/bmc.5309. [PMID: 34981527]
Xingyu Lu, Amila A Dissanayake, Chuqiao Xiao, Jie Gao, Mouming Zhao, Muraleedharan G Nair. The edible seaweed Laminaria japonica contains cholesterol analogues that inhibit lipid peroxidation and cyclooxygenase enzymes. PloS one. 2022 ; 17(1):e0258980. doi: 10.1371/journal.pone.0258980. [PMID: 35085233]
Kenneth Vanbrabant, David Van Meel, Anja Kerksiek, Silvia Friedrichs, Marco Dubbeldam, Melissa Schepers, Na Zhan, Katharina Gutbrod, Peter Dörmann, Hong-Bing Liu, Monique T Mulder, Tim Vanmierlo, Dieter Lütjohann. 24(R, S)-Saringosterol - From artefact to a biological medical agent. The Journal of steroid biochemistry and molecular biology. 2021 09; 212(?):105942. doi: 10.1016/j.jsbmb.2021.105942. [PMID: 34144153]
Ye-Jin Kim, So-Yeon Jeon, Jae-Sue Choi, Na-Hyun Kim, Yukiori Goto, Young-A Lee. Alterations of amygdala-prefrontal cortical coupling and attention deficit/hyperactivity disorder-like behaviors induced by neonatal habenula lesion: normalization by Ecklonia stolonifera extract and its active compound fucosterol. Behavioural pharmacology. 2021 06; 32(4):308-320. doi: 10.1097/fbp.0000000000000620. [PMID: 33491993]
Md Abdul Hannan, Abdullah Al Mamun Sohag, Raju Dash, Md Nazmul Haque, Md Mohibbullah, Diyah Fatimah Oktaviani, Md Tahmeed Hossain, Ho Jin Choi, Il Soo Moon. Phytosterols of marine algae: Insights into the potential health benefits and molecular pharmacology. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2020 Apr; 69(?):153201. doi: 10.1016/j.phymed.2020.153201. [PMID: 32276177]
I P Shanura Fernando, Thilina U Jayawardena, Hyun-Soo Kim, A P J P Vaas, H I C De Silva, C M Nanayakkara, D T U Abeytunga, WonWoo Lee, Ginnae Ahn, Dae-Sung Lee, In-Kyu Yeo, You-Jin Jeon. A keratinocyte and integrated fibroblast culture model for studying particulate matter-induced skin lesions and therapeutic intervention of fucosterol. Life sciences. 2019 Sep; 233(?):116714. doi: 10.1016/j.lfs.2019.116714. [PMID: 31376370]
Zhangfan Mao, Xiaoling Shen, Ping Dong, Gaoli Liu, Shize Pan, Xiangran Sun, Haifeng Hu, Li Pan, Jie Huang. Fucosterol exerts antiproliferative effects on human lung cancer cells by inducing apoptosis, cell cycle arrest and targeting of Raf/MEK/ERK signalling pathway. Phytomedicine : international journal of phytotherapy and phytopharmacology. 2019 Aug; 61(?):152809. doi: 10.1016/j.phymed.2018.12.032. [PMID: 31035050]
I P Shanura Fernando, Thilina U Jayawardena, Hyun-Soo Kim, Won Woo Lee, A P J P Vaas, H I C De Silva, G S Abayaweera, C M Nanayakkara, D T U Abeytunga, Dae-Sung Lee, You-Jin Jeon. Beijing urban particulate matter-induced injury and inflammation in human lung epithelial cells and the protective effects of fucosterol from Sargassum binderi (Sonder ex J. Agardh). Environmental research. 2019 05; 172(?):150-158. doi: 10.1016/j.envres.2019.02.016. [PMID: 30782534]
Nina S Liland, Karin Pittman, Paul Whatmore, Bente E Torstensen, Nini H Sissener. Fucosterol Causes Small Changes in Lipid Storage and Brassicasterol Affects some Markers of Lipid Metabolism in Atlantic Salmon Hepatocytes. Lipids. 2018 07; 53(7):737-747. doi: 10.1002/lipd.12083. [PMID: 30259993]
Pachiappan Perumal, Rajamani Sowmiya, Sundaram Prasanna Kumar, Sundaram Ravikumar, Paramasivam Deepak, Govindasamy Balasubramani. Isolation, structural elucidation and antiplasmodial activity of fucosterol compound from brown seaweed, Sargassum linearifolium against malarial parasite Plasmodium falciparum. Natural product research. 2018 Jun; 32(11):1316-1319. doi: 10.1080/14786419.2017.1342081. [PMID: 28637390]
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